Citation: Guo Bingbo, Shen Shengqiang, Jin Shuhui, Lu Huizhe, Zhang Jianjun. Synthesis and Enzyme Substrate Activity of p-Nitrophenyl N, N'-Diacetyl-4-thio-β-chitobioside[J]. Chinese Journal of Organic Chemistry, ;2019, 39(12): 3490-3497. doi: 10.6023/cjoc201906008 shu

Synthesis and Enzyme Substrate Activity of p-Nitrophenyl N, N'-Diacetyl-4-thio-β-chitobioside

School of Science, China Agricultural University, Beijing 100193

Corresponding author: Jin Shuhui, shuhuij@cau.edu.cn Zhang Jianjun, zhangjianjun@cau.edu.cn
Received Date: 10 June 2019
Revised Date: 31 July 2019
Available Online: 7 December 2019
Fund Project: the Chinese Universities Scientific Fund 2019TC135Project supported by the National Natural Science Foundation of China (No. 21772230) and the Chinese Universities Scientific Fund (No. 2019TC135)the National Natural Science Foundation of China 21772230

Figures(7)

Based on the resistance of glycosidase to the hydrolysis of glycosidase, the probe molecule p-nitrophenyl N, N'-diacetyl-4-thio-β-chitobioside (pNP-TCB) was designed and synthesized. The effects of pNP-TCB on the degradation of glycoside hydrolase family 18 (GH18) chitinase and 20 (GH20) β-N-acetylhexosaminidase were studied. The results showed that when pNP-TCB was combined with β-N-acetylhexosaminidase, the disaccharide substrate was hardly degraded. But when it reacted with chitinase, the pNP-TCB was degraded by enzyme to release p-nitrophenol group, and the corresponding ultraviolet absorption value can be detected by enzyme-labeled instrument at 405 nm. It indicates that the substrate molecule exhibits good specificity, which can be used to study the properties of GH18 chitinase at the cellular level without interference of β-N-acetylhexosaminidase. The pNP-TCB can also provide a good detection method for screening and isolation between the GH18 chitinase and the GH20 β-N-acetyl hexose.
- p-nitrophenol,
- disaccharide substrate,
- chitobioside,
- chitinase,
- UV absorption
1. [1]
  Lai, K. P. Pharm. Today 2009, 19, 14(in Chinese).
2. [2]
  Zhu, K. Y.; Merzendorfer, H.; Zhang, W. Annu. Rev. Entomol. 2016, 61, 177. doi: 10.1146/annurev-ento-010715-023933
3. [3]
  Zechmeister, L.; Toth, G. Z. Physiol. Chem. 1934, 223, 53. doi: 10.1515/bchm2.1934.223.1-2.53
4. [4]
  Liu, T. Ph.D. Dissertation, Dalian University of Technology, Dalian, 2009 (in Chinese).
5. [5]
  Dahiya, N.; Tewari, R.; Hoondal, G. S. Appl. Microbiol. Biotechnol. 2006, 71485, 773.
6. [6]
  Alton, M. Adv. Enzymol. Relat. Areas Mol. Biol. 1987, 59, 59.
7. [7]
  Liu, T.; Chen, L.; Ma, Q.; Shen, X.; Yang, Q. Curr. Pharm. Des. 2014, 20, 754. doi: 10.2174/138161282005140214164730
8. [8]
  Macdonald, J. M.; Tarling, C. A.; Taylor, E. J.; Dennis, R. J.; Myers, D. S.; Knapp, S.; Davies, G. J.; Withers, S. G. Angew. Chem., Int. Ed. 2010, 49, 2599. doi: 10.1002/anie.200906644
9. [9]
  Chen, L.; Liu, T.; Duan, Y. J. Agric. Food Chem. 2017, 65, 3851. doi: 10.1021/acs.jafc.7b01710
10. [10]
  Schüttelkopf, A. W.; Andersen, O. A.; Rao, F. V. ACS Med. Chem. Lett. 2011, 2, 428. doi: 10.1021/ml200008b
11. [11]
  Dong, L. L.; Shen, S. Q.; Chen, W.; Lu, H. Z. Bioorg. Med. Chem. 2019, 27, 2135
12. [12]
  Shen, S. Q.; Chen, W.; Dong, L. L. J. Enzyme Inhib. Med. Chem. 2018, 33, 445. doi: 10.1080/14756366.2017.1419217
13. [13]
  Shen, S. Q.; Dong, L. L.; Chen, W. J. Agric. Food Chem. 2019, 67, 6387. doi: 10.1021/acs.jafc.9b02281
14. [14]
  Boller, T.; Mauch, F. Methods Enzymol. 1988, 161, 430. doi: 10.1016/0076-6879(88)61052-4
15. [15]
  Ohtakara, A. Methods Enzymol. 1988, 161, 426. doi: 10.1016/0076-6879(88)61051-2
16. [16]
  Cabib, E. Methods Enzymol. 1988, 161, 424. doi: 10.1016/0076-6879(88)61050-0
17. [17]
  Koga, D.; Yoshioka, T. Agric. Biol. Chem. 1998, 62, 1643
18. [18]
  Zhou, J. S.; Chen, L. L.; Kang, L. Q.; Liu, Z. H.; Yuan, S. J. Agric. Food Chem. 2018, 66, 12773. doi: 10.1021/acs.jafc.8b04261
19. [19]
  Duivenvoorden, B. A.; Ghauharali, K.; Scheij, S. Carbohydr. Res. 2014, 399, 26. doi: 10.1016/j.carres.2014.07.007
20. [20]
  Dong, L. L.; Shen, S. Q.; Lu, H. Z.; Jin, S. H.; Zhang, J. J. ACS Sens. 2019, 45, 1222.
21. [21]
  Krolicka, M.; Hinz, S. W. A.; Koetsier, M. J. J. Agric. Food Chem. 2018, 66, 1658. doi: 10.1021/acs.jafc.7b04032
22. [22]
  Van, Munster. J. M.; Dobruchowska, J. M.; Veloo, R. Appl. Microbiol. Biotechnol. 2015, 99, 2209. doi: 10.1007/s00253-014-6062-3
23. [23]
  Wang, S.; Moyne, A. L.; Thottappilly, G.; Wu, S. J.; Locy, R. D.; Singh, N. K. Enzyme Microb. Technol. 2001, 28, 492. doi: 10.1016/S0141-0229(00)00362-8
24. [24]
  Rich, J. R.; Dr, A. S.; Dr, M. M. P. Angew. Chem. 2004. 116, 623. doi: 10.1002/ange.200352606
25. [25]
  Driguez, H. ChemBioChem 2001, 2, 311 doi: 10.1002/1439-7633(20010504)2:5<311::AID-CBIC311>3.0.CO;2-L
26. [26]
  Xu, Y. R.; Zhang, J. J.; Dong, Y. H.; Tan, W. M. Chin. J. Org. Chem. 2017, 37, 2929(in Chinese).
27. [27]
  Jiang, R.; Zong, G.; Liang, X.; Jin, S.; Zhang, J.; Wang, D. Molecules 2014, 19, 6683 doi: 10.3390/molecules19056683
28. [28]
  Jiang, R.; Liang, X. M.; Sun, J.; Zhang, J. J.; Wang, D. Q. Chin. J. Org. Chem. 2014, 34, 926(in Chinese).
29. [29]
  Wang, J. Y.; Jiang, R.; Liang, X. M.; Wang, D. Q.; Zhang, J. J. Chin. J. Org. Chem. 2017, 37, 375(in Chinese).
30. [30]
  Wang, L. X.; Lee, Y. C. J. Chem. Soc. 1996, 27, 581.
31. [31]
  Chen, H. M.; Withers, S. G. Carbohydr. Res. 2007, 342, 2212. doi: 10.1016/j.carres.2007.05.023
32. [32]
  Davis, B. G. EP 1644390 2005[Chem. Abstr. 2005, 142, 94064].
33. [33]
  Chupakhina, T. A. Russ. J. Bioorg. Chem. 2004, 30, 301. doi: 10.1023/B:RUBI.0000030138.26142.4b
34. [34]
  Loft, K. J. ChemBioChem 2009, 10, 565. doi: 10.1002/cbic.200800656
35. [35]
  Nikolaev, A. V.; Ivanova, I. A.; Shibaev, V. N. Bioorg. Khim. 1990, 16, 1693.
36. [36]
  Fettke, A.; Peikow, D.; Peter, M. G. Tetrahedron 2009, 65, 4356. doi: 10.1016/j.tet.2009.03.067
37. [37]
  Nawani, N. N.; Kapadnis, B. P. J. Appl. Microbiol. 2010, 90, 803.
38. [38]
  Nguyen, H. A.; Nguyen, T. H. J. Agric. Food Chem. 2012, 60, 3475.
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